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Award ID contains: 1900594

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  1. ; ; ; (, Organic Letters)
  2. ; (, Journal of the American Chemical Society)
  3. ; (, Journal of the American Chemical Society)
  4. ; (, Organic letters)
    Gaich, T. (Ed.)
    We report the cycloaddition reactions of 1-alkoxy-1- amino-1,3-butadienes. These doubly activated dienes are prepared on a multigram scale from crotonic acid chloride and its derivatives. The dienes undergo Diels−Alder (DA) and hetero-Diels−Alder (HDA) reactions under mild reaction conditions with a variety of electron- deficient dienophiles to afford cycloadducts in good yields with excellent regioselectivities. The hydrolysis of the DA cycloadducts provides 6-substituted and 6,6-disubstituted 2-cylohexenones, which are versatile building blocks for complex molecule synthesis. The corresponding HDA cycloadducts afford 6-substituted 5,6-dihydropyr- an-2-ones. 
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